Maryland not only has a multitude of popular sailing locations, such as Chesapeake Bay and Annapolis, but it is also offers many different variations of sailing. You can listen to a local musician on board, do a team building challenge with your company, participate in a regatta, or sail into the sunset while learning about Maryland’s history. Here are our seven best places to go sailing in Maryland.


These 7 Maryland Destinations Are Perfect For Sailing



1. Chesapeake Bay

Schooner Woodwind has weekly sailboat races through the Chesapeake Bay on Wednesday nights from late spring to the end of August. On Thursday nights you can go on a sunset sailing trip while listening to a live, local acoustic musician. If you’re a history buff, go sailing on Monday nights when the company has speakers who teach you about the history of the Chesapeake Bay and Annapolis areas of Maryland.

Find a place to stay on the Chesapeake Bay, Maryland


2. Havre De Grace

In Havre De Grace, Maryland you can take professional sailing lessons, rent a sailboat for a week, or host a corporate event to improve your company’s culture and team building skills. If you are planning to sail frequently and looking to save money, the company

BaySail has a sailing membership program called SailTime. BaySail has also been voted one of the top sailing schools by the American Sailing Association.

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3. Annapolis

If you have your own sailboat, a great place to secure your boat is the Port Annapolis Marina. The marina offers bridge-free access to the Chesapeake Bay. After sailing, go swimming in the outdoor pool, have a cookout at the gazebo, or go checkout the historic downtown area.

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4. Rock Hall

In Rock Hall you can rent a luxury yacht from a company such as Haven Charters. There are endless options of where you can go sailing from Rock Hall. For example, you can go along the Severn River, Miles River, West River, or Rhode River.

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5. Gibson Island

Many sailing legacies started out on Gibson Island. The Gibson Island Yacht Squadron holds many popular annual regattas. At Gibson Island you can also participate in weekly races in the Magothy River, enroll your kids in the Junior Fleet Program, or go on an organized cruise.

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6. Baltimore

Located on Sue Island, the Baltimore Yacht Club is a popular sailing spot in Baltimore. The club has a wide range of annual activities, such as holiday meals, festivals, cocktail parties, and fireworks.

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7. Deep Creek Lake

Swanton is a great place for kids and adults to learn how to sail since it is home to the Deep Creek Sailing School. The school has US Sailing certified instructors and offers private or group lessons June through August.

Find a place to stay on Deep Creek Lake, Maryland





This article was written by Colleen Regan.